How Much Money Is Enough? Plus, Why AI Won’t Replace Financial Advisors — with Jack Raines

Summary

Podcast Summary: The Prof G Pod with Scott Galloway

Episode: How Much Money Is Enough? Plus, Why AI Won’t Replace Financial Advisors — with Jack Raines
Date: July 27, 2026
Host: Scott Galloway
Guest: Jack Raines, writer of the Young Money newsletter

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Overview

In this special episode focused on personal finance, Scott Galloway is joined by Jack Raines, author of "Young: A Field Guide to Wealth and Purpose in Your Twenties." Together, they tackle three core questions submitted by listeners:

1. Is there such a thing as "enough" wealth?
2. How should young people save for a home in high-cost cities?
3. Will financial advisors be replaced by AI?

The discussion is frank, practical, and sprinkled with witty quips, making financial wisdom both approachable and actionable.

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Key Discussion Points & Insights

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1. Is There Such a Thing as "Enough" Wealth?

[02:01–07:07]

• Status Chasing and Mimetic Desire

  • Jack Raines: "Humans are kind of status chasing monkeys where like once you get to what you thought was enough, there's always another level." (02:22)
  • He discusses how "enough" is subjective and depends on resisting the urge to continually compare oneself to people with more.
  • Growing up in South Georgia, his perspective of "enough" changed dramatically after moving to New York and San Francisco.

• Practical Formula for Enough

  • Scott Galloway: “If you take your annual burn times 20, that's when you sort of financially are probably set right and can start to enjoy life.” (03:13)
  • Observes that hoarding wealth is common, especially in America, and that “hoarding wealth is a virus that infects America.” (03:13)
  • Encourages enjoying wealth and spending appropriately, especially as people age.

• The Happiness Question

  • Scott debunks the myth that billionaires are less happy than millionaires but emphasizes that past a certain point, more wealth does not buy more happiness.

• Behavioral Biases & Spending in Retirement

  • Jack Raines references Nick Maggiulli’s research showing most retirees spend less than anticipated and often accumulate more wealth unnecessarily:
    • "It's actually an inefficient use of money if you have, like, several million saved up...you probably should have spent some sooner." (05:25)
  • The “scarcity mindset” can be self-defeating; enjoying money at each stage of life is important.

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2. Should Young People Save for a House in a High-Cost City?

[07:07–14:27]

• Do You Even Want to Buy?

  • Jack Raines: "First question is, do you even want to?" (07:18)
  • He highlights the sky-high costs in cities like San Francisco and New York, citing $3 million as the going rate for a family-sized home.
  • Suggests renting while young, making money, and waiting until a move to the suburbs is more practical, particularly if planning to raise a family.

• The Math of Buy vs. Rent

  • Scott Galloway:
    • "The American dream is brought to you by the National Association of Realtors, who always find a reason for you to keep just buying..." (08:29)
    • Points out renting can often make more sense in expensive cities, warning against becoming "house poor."
    • Notes the psychological benefits of home ownership, especially for families, but warns against the financial and emotional pitfalls.

• Home Ownership, Policy, and Wealth Transfer

  • Scott Galloway:
    • "Housing has been a transfer of wealth from the entrance to the incumbents where they create artificial scarcity..." (10:56)
    • Calls for “build, baby, build” policies to address the housing shortage and advocates for YIMBYism (Yes In My Backyard).

• Financial Nihilism Among Young People

  • Scott observes:
    • “A lot of kids or young people are saying, there's no fucking way I can buy a home. I'm just, I'm going to go to Coachella.” (12:41)
  • Jack Raines:
    • Recognizes "a little bit of financial nihilism where people are like, I'll never afford a home, at least not in one of these two cities. So why not blow it on, you know, material goods, consumerism, experiences..." (13:23)
  • Housing supply is further squeezed by family wealth subsidizing down payments for some, exacerbating inequities.

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3. Will Wealth Advisors Survive AI?

[17:59–24:01]

• The Enduring Need for Human Advisory

  • Jack Raines:
    • “You don't get a wealth advisor to help you outperform the market...Wealth advisors are really there to like tell you what not to do and to fix behavioral problems.” (18:07)
    • During downturns, advisors prevent panic sales and emotional mistakes.

• Role of Financial Advisors Beyond Investments

  • Scott Galloway:
    • Uses advisors less for stock picks and more for “diversification, tax efficiency...and then things like trusts...” (19:13)
    • Cautions against high-fee products, advocates for low-cost index funds.
    • Highlights the current and coming shortage of financial advisors, leading to high demand despite advances in AI.

• AI as an Enhancement, Not Replacement

  • AI provides access and automation but lacks contextual nuance, behavioral support, and personalization:
    • "The quality of what AI tells you is based on the quality of the prompt which...is based on your financial literacy." (19:13)
    • AI currently exhibits biases, such as giving more conservative advice to women, impacting outcomes.

• Relationship-Driven Professions Will Endure

  • Jack Raines:
    • “At the end of the day it's always going to be a relationship game...you can't just replace human relationships with technology.” (23:24)
    • Optimistic about relationships and emotional support as enduring value in wealth advice.

• Career Advice for Advisors

  • Scott Galloway:
    • “Being a financial advisor is the worst job in the world for 10 years...And then after 10 years...it becomes the best business in the world.” (22:28)
    • Stresses network-building and relationship management as the keys to long-term success in financial advising.

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Notable Quotes & Memorable Moments

• On Enough Wealth:

  • Jack Raines: “Is there an upper limit to wealth? No. Is there enough wealth? Yes. Depending on, like, where you set your standards...” (02:40)

• On the Housing Market:

  • Scott Galloway:
    • “Housing has been a transfer of wealth from the entrance to the incumbents where they create artificial scarcity...” (10:56)
    • “When I was your age, every dollar I had was going towards a little fund where I could save $60,000 for the down payment on a home. And now...a lot of kids...are saying, there's no fucking way I can buy a home. I'm just, I'm going to go to Coachella.” (12:38)

• On Advisors vs. AI:

  • Jack Raines:
    • “You don't get a wealth advisor to help you outperform the market...wealth advisors are really there to tell you what not to do and to fix behavioral problems.” (18:07)
  • Scott Galloway:
    • “I didn't use a financial advisor...to get wealthy. I use them now to stay wealthy.” (19:23)
    • “Everything still comes back to the core skill, which seems to be the most enduring and that is the ability to establish relationships.” (24:01)

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Important Timestamps

• [02:01] – What is “enough” wealth?
• [07:07] – Should young people save for a home in a big city?
• [10:56] – Wealth transfer, YIMBY vs. NIMBY, housing policy
• [12:38] – Birth rates, home ownership, generational shifts in priorities
• [17:59] – Will AI replace wealth advisors? The behavioral value of advisory
• [22:28] – The career arc of financial advisors
• [24:01] – The enduring value of relationships in finance

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Conclusion

Scott Galloway and Jack Raines deliver actionable, nuanced perspectives on wealth, real estate, and the future of financial advice. They emphasize the importance of defining personal "enough," urge strategic thinking about major life purchases, and agree that no technology can replace the human element in financial guidance. The episode leaves listeners with clear-eyed advice and memorable soundbites, whether you’re mapping your financial future or simply trying to figure out when, and if, you’ve arrived at “enough.”

Transcript

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[Scott Galloway]

Welcome to Prophet G on Personal Finance, a special episode where we're joined by Jack Rains, writer of the Young Money newsletter and author of Young A Field Guide to Wealth and Purpose in your twenties. Together we'll discuss whether there's such a thing as enough wealth, how young people should save for a house in a high cost city, and whether wealth advisors survive. AI Jack, welcome.

[Jack Raines]

Happy to be here. Thanks for having me.

[Scott Galloway]

Scott, thanks for being here. Everyone was really excited to have a young, knowledgeable financial person on. All right, let's bust right into it. Question 1 Our first question comes from Natanya Cranford on Instagram. Is there such a thing as enough wealth? I still fly economy, but I can fly anywhere I want. Jack, is there such a thing as enough wealth?

[Jack Raines]

So I mean, I think the answer is yes there is. The issue is humans are kind of status chasing monkeys where like once you get to what you thought was enough, there's always another level. So like, it's a question of like, like I'm from, I'm from South Georgia, right? So my version of enough wealth growing up is a lot different. Than having lived in New York or San Francisco for the last four years. So, I mean, my, my answer to that is like, yes, there is. The question is like, can you resist the, like, chasing people who are one level ahead of you? Because is there an upper limit to wealth? No. Is there enough wealth? Yes. Depending on, like, where you set your standards for what enough means. You know, for some people, it's like several hundred thousand, a few million tens of millions, but it's much more. Can you resist just like chasing after other people that you view to be a little bit ahead of you?

[Scott Galloway]

Yeah, I think about this a lot. I mean, on a very practical level, if you take your annual burn times 20, that's when you sort of financially are probably set right and can start to enjoy life. And also, I think a lot of people make a mistake. I had some questions from some people who are retired about how much money. Then I'm asked about their life. I'm like, you should be spending more money. You know, you're not. Unless you really do something stupid, you're fine. And you got. My sense is you guys don't travel, you know, spend some money, order the good wine. And I think about this a lot. I think hoarding wealth is a virus that infects America. I just don't think there's any reason to have over a certain amount of wealth. I don't think you're going to get much happiness, if any incremental happiness. I don't think you'll be less happy. I think this notion that billionaires are less happy than millionaires is also a. A myth. But what you said, what is it? Humans are mimetic. And that is we don't think about satisfaction from what we have. We compare ourselves to others. And I have more money than most citizens, but I would like. And I stopped aggregating wealth or purposely trying to aggregate wealth after about 10 years ago. I either spend it or I give it away now. But I still occasionally regret not going more in on AI and trying to become a billionaire. Because I would like to fund npr. I would like to have more political influence. Influence and candidates. You can always find reasons. I still feel insecure. And I would love to have you live in a capitalist society. No matter how wealthy you are, they're always going to create incentives to want more, to keep you working right and keep you productive. But I do think there's an art to saying, at some point, I, at a minimum, want to focus on my relationships and get off this hamster wheel. And it's not easy. And by the way, that's a story of privilege, because I think the vast majority of people are just trying to figure out a way to save enough to send their kids to college and not have medical debt. But yeah, that word enough is so powerful, and it's consciously deciding yourself when is enough and what would happen if I were fortunate enough to get to enough. Any closing thoughts on this?

[Jack Raines]

Yeah, I mean, there's. I have two things to add. One, do you know Nick Magiulli? Um, anyway, he had, in a blog post like, four or five years ago, had a really interesting stat talking about how, like, you know, most people are worried about not having enough money in retirement, but most Americans actually are spending less than, like, they are. They're earning more each year than what they're actually spending down in retirement. So to your point of, like, hoarding wealth being a virus, I think it's actually an inefficient use of money if you have, like, several million saved up and there's just no chance, like, even accounting for what you want to leave for your kids or grandkids. If you're rapidly accumulating more and more money just from compounding and you're seven 70s and 80s that you can't spend down, you probably should have spent some sooner. And the other. The other point I have on that is, like, the whole point of wealth at the end of the day is somebody has to spend it on something, whether it's you, your kids, you give it away to, like, a philanthropic organization to spend. And having, like, a scarcity mindset where you're constantly worried about not having enough, even when you objectively have enough, is just depriving yourself of things you could spend money on to enjoy. Again, whether it's material things, experiences, relationships, and like, the. The things that you can spend that money on, that you will enjoy are just going to change a lot. Like, the thing you'll enjoy at 25 is different from 35 or 45 or whatever. So I actually think one of the hardest things is like, being willing to spend some money in your 20s when you probably don't have as much, knowing that, like, you'll keep compounding over time, right? But it's tough. It's like, it's a very tough thing to spend money when everybody else is still making money. And thinking through, like, our idea of what we're going to need later is always so much higher than what it actually is. I think.

[Scott Galloway]

Fair enough. All right, let's. Let's head on to question number Two. It also comes from Instagram. J. Kim asks, how should young people go about saving for a house in a high cost of living city? Jack.

[Jack Raines]

So I think the first question is, do you even want to? Because there's a lot of people who will move to New York or especially Stephanie Cisco now with the AI boom where like I lived in SF last year and the going rate for like a decent studio apartment is around probably $4,000. Now that's for a, you know, 500 square foot shoebox. So the question is, okay, you can make the math work on that, but then you get married and you want to have kids and all of a sudden you probably need at least a three bedroom home, which is going to cost like if you're actually in San Francisco proper, probably $3 million. I was looking at some three bed, two baths in New York to like prep for this same thing. Call it $3 million minimum in a decent neighborhood. And then if you're doing that, okay, are you going to pay for private school and what's that going to cost? Are you going to have a car? What's the parking going to cost? Like you, you end up in this thing where you're going to be spending so much money per year to keep up. The first question to ask is, should you even buy a home in like New York or San Francisco or should you live there to make money, meet your spouse, like save cash and rent. And then once you're at the point that you're having kids or thinking about school, you move to the suburbs or you move to New Jersey or Long island or pick your version of that.

[Scott Galloway]

Yeah, look, I think you're right. I think it's important to do the math that this, you never lose money in real estate. The American dream is brought to you by the national association of Realtors, who always find a reason for you to keep just buying and give them their 5 or 6% commission. There are a lot of instances where it doesn't make any sense to. Unless you just have a lot of money.

[Jack Raines]

Yep.

[Scott Galloway]

To buy versus rent. New York and San Francisco, almost always it makes more sense to rent. And there is a certain, you know, elegance to renting and slamming your keys down and being economically mobile because what you don't want is to end up underwater on your mortgage or to be house poor and just so focused on making your mortgage that you can't enjoy life. I do think at some point, I mean, I'm torn on this because while as an asset class, homes have done the same or even maybe Slightly underperformed the broader market. It is a great way to build wealth because people have a tendency to make that mortgage payment as opposed to maybe spending two or $3,000 saving and buying stocks. They have a tendency to make that payment. Also, I think there are some real psychic benefits, specifically moving towards a family or mating or having kids and procreating, which I think are rewarding. And that is, I really was fascinated by the study that said that housing prices are a form of birth control. And that is for every 10% housing prices go up, the birth rate has declined by 1%. Because I mean you're, you're a kid, Jack. But generally what you find is when you buy a house, you start fixing it up and you start fixing up a second bedroom and decide, well, maybe we should find someone to live in the second bedroom. Yeah, I know, let's, let's, let's pull the goalie and have a kid. Right? Yeah, yeah. So. And I think generally speaking, that's good for you, good for your wealth, good for your marriage. Well, I don't want to tell people, let me be clear. You can't save a marriage having kids. That's probably not the thing to do. But I do think there is psychological return, psychic return and home ownership. And that I think a decent policy. I met with a Democratic senator this morning. A lot of people think is running for president. I mean, it's at a drill, baby drill. It should be build, baby build. And we should have tax incentives that unleash the private homebuilder sector and, and yimby laws such that we go back to where I was. I was living in San Francisco out of business school. I bought a two bedroom house in Potero Hill for $285,000. The average graduate of the Haas School of business in 1992 was making 100 grand. So it was 2.8 times my salary. Now the average Haas grad is making 200 grand, which is a great income. But the average home I think in the Bay Area as of last year was 2.2 million. It's probably closer to 3 now because you've seen this acceleration. So what is that? 15? It's gone from 2.8 to 15 times. And like so many things in our society, housing has been a transfer of wealth from the entrance to the incumbents where they create artificial scarcity through sequestering housing permits by putting housing permits or the authority in the house of current homeowners. This is an instance where it should go back to bureaucrats. You need growth, you need more housing. And people like you are having a tough time finding a house because people like me get very concerned with traffic and make it more difficult to build more housing such that the price of my house goes up in value. I think this is a big issue for America. You need a kitchen cabinet of people who can sit down with you and say, all right, give me the math, give me the numbers. Should you buy a house? Should you not? And even if it doesn't make economic sense, if you got rich parents and you got a dude you want to marry, buy a house. There's a lot of nuance here. And I think people, this is one of those things where people will spend so much time deciding which iPhone they're going to buy and they don't spend enough time for 1,500 bucks. They don't spend enough time thinking about what is arguably the largest purchase of their of their life. I also think, and I'm sorry for the word salad here, that the IRL movement, where Live Nation is booming and Taylor Swift tickets are going for, you know, $6,000, is that a lot of people of your generation have just given up on saving for a home. When I was your age, every dollar I had was going towards a little fund where I could save $60,000 for the down payment on a home. And now I think a lot of kids or young people are saying, there's no fucking way I can buy a home. I'm just, I'm going to go to Coachella.

[Jack Raines]

I mean. Well, something else that's funny that you hinted on there was, and I totally agree on the like, YIMBY versus nimbyism. At the end of the day, we should build more homes and then people could like afford to move into a home. But a lot of the voters don't want their home prices to drop because of what we were saying earlier about it. A lot of people treat it like an investment asset. You don't want your $4 million home to be worth 2.5 million. Even if a lot of 26 year olds come in, buy homes. But this is especially true in New York. So much of the housing is like subsidized by people who do have rich parents. Like, you know, like, I didn't really pick up on this until like, I, I also went to business school. I was at Columbia. And like, you have people who are taking out a couple hundred thousand dollars in student loans. You have people who are like, fine, but not like trust fund kid. And then you have people whose lifestyle subsidized or, like, parents will, like, buy them an apartment or townhouse, and everybody's competing for the same housing supply. So, like, for the, I guess for the people who are, like, making their own down payment for a home right now in a high cost of living city, so much of the already scarce supply is also subsidized by, like, family income, which I'm, like, all for. Like, if your parents can, like, support and help with, like, big life costs, awesome. But it makes that really tight supply even tighter. So it's just tough. You have, like, a really tough supply demand market. You have a lot of factors against you. And yeah, there's a little bit of financial nihilism where people are like, I'll never afford a home, at least not in one of these two cities. So why not blow it on, you know, material goods, consumerism, experiences, and it's just a pretty vicious cycle.

[Scott Galloway]

Okay, so we'll be right back after a quick break.

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[Scott Galloway]

welcome back. We're here with Jack Rins. Question number three comes from Cordova Texas. Will there be a need for wealth advisors as AI tools develop over time?

[Jack Raines]

Oh yeah, 100, a hundred percent. I mean like you don't, you don't get a wealth advisor to like help you outperform the market. There's a million like agencic AI things. Robin Hood just rolled out some AI agent trading tool like to actually place trades. Yeah, AI can do it but wealth advisors are really there to like tell you what not to do and to fix behavioral problems. Market tanks you Panic. You want to sell like the amount of people who would have sold the bottom in 2020 when the market tanked or would have sold in 2022, Q4 when like the NASDAQ was cratering. Where if they had a financial advisor who was like, stay the course. If anything, like increase your contributions now while stocks are on sale. You know, for somebody who would have like impulse sold because they panicked, they would have missed out on the market doubling from those bottoms. So I actually think there's more and more and more noise that's causing people to feel more and more distracted when it comes to investing. And having a professional that can actually just manage your emotions and stop you from making like behavioral screw ups is more important now than it was at any other point because of like so much noise on social media.

[Scott Galloway]

Yeah, it's, it's interesting. About 3/4 of Gen Z and 2/3 of millennials seek financial advice online or via social media. And only 1 in 7 Gen Z say they would turn to a financial professional first when faced with a question about finances compared with 39% of boomers. What's interesting is that. Well, let me go to your point. I have found I didn't use a financial advisor. Maybe I should have, but I didn't to get wealthy. I use them now to stay wealthy. And that is, I'm not really interested in their stock recommendations. I just don't think they know any more, any less than me about stocks. And also to be fair, I think some of these guys are pushing their internal funds which tend to have higher fees. And I think fees are the enemy of compounding returns. Be on low cost index amounts. You want to be diversified. I spend a lot of money on financial advisors, but mostly it's about diversification, tax efficiency, which is Latin for legal tax avoidance, and then things like trusts and trying to figure out a way like that. I give my kids enough money someday such that they can do anything, but not enough money so they can do nothing. You know, if you're blessed with some level of economic security, you want advice on how to be smart, how not to lose it, to find out if you're too concentrated. Should I be, oh, I should sell, I need money, Should I sell these stocks? A financial advisor might say, no, don't sell the stock, borrow against it and let it continue to compound because we can borrow against your stocks, you know, 10, 20% of their worth and not be that worried about getting too over levered. And you don't have to pay taxes on your gains. I mean there's just, it makes sense. Once you have a certain amount, use AI, but use it to inform you and then talk to people who understand money, whether it's a financial advisor or just other rich people who really understand how to invest money. What's interesting is that while AI, I'm an AI optimist and think it's going to create more jobs than it destroys and I think you're going to have more financial advisors and in 10 years than you have now and there's going to be a shortage. Nearly 40% of financial advisors are expected to retire within a decade, creating a shortfall of roughly 100,000 professionals. And AI tools may not struck, you know, may be structurally required to step in and fill the gap for retail guidance. But these LLMs have, you know, they have real biases and they're generally not good at giving long term financial advice. And the quality of what AI tells you is based on the quality of the prompt which, which is based on your financial literacy. Younger people who are not as financially literate are asking a like how can I get 10x my money in the next 12 months? And it'll come back. It'll say look, that's unlikely but the most volatile assets are crypto and try this. So a lot of it's prompt it also there's a study showing that these LLMs appear to be sexist and that their recommendations tend to be more conservative towards women than men, resulting in them not making over the long term as much much money in some. I think it'll be an enhancement, it'll make financial advice more accessible, which is great and it's a good thing about AI but it won't replace human advisors since the quality of guidance depends on who you are and context and nuance and tax. I think we're actually going to see more financial advisors and I would say that it's probably with the right credentialing, understanding accounting very much you need to understand tax if you have good relationship skills, if you're good at networking, if people know being a financial advisor is the worst job in the world for 10 years because it means to going every fucking event and kissing everyone's ass and sitting them down and talking to them about their financial future and being their therapist when the market goes down. And then after 10 years, if you can survive it that long and build a book, it becomes the best business in the world because you basically have an asset base of people who keep paying you 10, 20, 50, 100 basis points on the assets under management portfolios

[Jack Raines]

keep going that way hopefully.

[Scott Galloway]

Right, Hopefully. But any closing thoughts on the career prospects of someone thinking of being a financial advisor?

[Jack Raines]

Yeah, I think it's one of those things where at the end of the day it's always going to be a relationship game and something that a lot of the Silicon Valley world misses is you can't just replace human relationships with technology. You can like amplify a lot of stuff, but when people are in like, markets are volatile, people are emotional, they both like, they want like a comforting voice to rely on on stuff or somebody walking back from the cliff. So, you know, I, my real advice is it isn't about like, should you go into this job or that job or whatever, but just don't like. I would not be pessimistic about AI's impact on relationship driven industries. You know, financial advice being one of those.

[Scott Galloway]

Yeah. So again, everything about everything still comes back to the core skill, which seems to be the most enduring and that is the ability to establish relationships. Jack Raines is the writer of the newsletter Young Money and author of the forthcoming book Young A Field Guide to Wealth and purpose in your 20s. Who's holding it up? Jack, thanks so much for joining us and congratulations on your success.

[Jack Raines]

Thank you. Thanks for having me.

[Scott Galloway]

This episode was produced by Jennifer Sanchez and Laura Gennar. Cami Reek is our social producer, Brad Williams is our editor, and Drew Burrows is our technical director. Thank you for listening to the propsheet pod from Propstream Media.

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